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B&B in Westchester

The Sono Chicago

3.5 star property
Near North Side
10.0 out of 10, Exceptional, (482)
"Great location and hospitality! "
United States
Teresa
The price is AED 480
AED 564 total
includes taxes & fees
17 Nov - 18 Nov
The Sono Chicago

The Publishing House B&B

3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (187)
"This was my first time ever booking at a bed & breakfast and it was amazing!!! The staff were so helpful & great. The breakfast was very delicious. My room was perfect & clean. Everyone was so lovely. Can’t wait to go back!!!"
United States
Jazmine
The price is AED 714
AED 806 total
includes taxes & fees
7 Dec - 8 Dec
The Publishing House B&B

Dorothy's

3.0 star property
Lakeview
8.4 out of 10, Very Good, (93)
"Halsted is a nice neibourhood. We liked the secondhand shops."
United States
Lisa
The price is AED 149
AED 303 total
includes taxes & fees
17 Nov - 18 Nov
Dorothy's

The Villa Toscana

2.5 star property
Lakeview
7.8 out of 10, Good, (619)
"We "
United States
Brian
The price is AED 135
AED 306 total
includes taxes & fees
17 Nov - 18 Nov
The Villa Toscana

House 5863 - Chicago Bed and Breakfast

3.5 star property
Edgewater
9.0 out of 10, Wonderful, (491)
"Easy check-in, c. Easy parking. "
United States
Jordan
The price is AED 376
AED 640 total
includes taxes & fees
17 Nov - 18 Nov
House 5863 - Chicago Bed and Breakfast

Wicker Park Inn

3.5 star property
West Town
9.0 out of 10, Wonderful, (256)
"My husband and I loved our stay. The room was beautiful, clean, and comfortable. Being able to stay in a neighborhood inn made our trip to Chicago memorable. We went to the Wicker Park Farmer's Market, ate at local restaurants, hung out at local bars, met cool people, and just enjoyed being part of the city. "
United States
Melissa
Wicker Park Inn

Villa D' Citta

3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (110)
"Would stay again anytime!!"
United States
Dominic
The price is AED 756
AED 888 total
includes taxes & fees
1 Dec - 2 Dec
Villa D' Citta

Ray's Bucktown B&B

3.5 star property
Bucktown
9.8 out of 10, Exceptional, (381)
"Ray's is such a fun, quirky place to stay - tons of creativity has gone into making it a unique stay. The breakfast is fabulous, on-site parking is convenient, and there is excellent attention to safety and security. I thoroughly enjoyed my stay and look forward to visiting again!"
United States
Tala
The price is AED 599
AED 676 total
includes taxes & fees
17 Nov - 18 Nov
Ray's Bucktown B&B

Harvey House Bed & Breakfast

4.0 star property
Oak Park
9.8 out of 10, Exceptional, (119)
"Beautiful home, welcoming host."
United States
scott
The price is AED 848
AED 942 total
includes taxes & fees
17 Nov - 18 Nov
Harvey House Bed & Breakfast

Five bedroom - 3 bath - Sleeps 12

Lakeview
The price is AED 1,818
AED 3,212 total
includes taxes & fees
2 Dec - 3 Dec
Five bedroom - 3 bath - Sleeps 12
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Westchester Hotel Reviews

Frequently asked questions

Searching for B&Bs in Westchester?
Whether you're on a family vacation and want a small, cozy place to stay, or you're traveling solo and hoping to meet fellow tourists, B&Bs can be a great choice for many travelers. If you're interested in discovering some top attractions, Wrigley Field and Michigan Avenue are worth a stop.
Why consider B&Bs instead of traditional hotels?
With attentive service, opportunities to mingle with other guests, and of course a full breakfast to start the day, B&Bs offer a truly one-of-a-kind environment.
What are the best B&Bs in Westchester?
Here are some well-liked B&Bs in the area: Dorothy's: 7 rooms. 13.6 mi (21.9 km) from the heart of Westchester.The Villa Toscana: 9 rooms. 13.6 mi (21.9 km) from the downtown core. House 5863 - Chicago Bed and Breakfast: 7 rooms. Situated 14.7 mi (23.6 km) from the heart of Westchester. Enjoy the designer toiletries and private yard. The Sono Chicago: 7 rooms. 13 mi (20.9 km) from the heart of downtown. Enjoy the rooftop terrace and fireplace in the lobby. Ray's Bucktown B&B: 11 rooms. Located 11.3 mi (18.2 km) from the core of Westchester. Enjoy the free cooked breakfast and rooftop terrace.
What's the best time of year to book my B&B in Westchester?
When you're planning your getaway to Westchester, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 71°F, while the coldest months are January and February with an average of 31°F. The snowiest months in Westchester are January, November, February, and December, with each month seeing an average of 5 inches of snowfall.
What is there to do in Westchester?
Travelers enjoy Westchester for its restaurants and shopping. You might also consider a trip to sites like Wrigley Field or Michigan Avenue if you have time to see more of the area.
How can I get to and around Westchester?
You can map out your trip in and around Westchester ahead of time with these transportation options. Fly into Chicago Midway Airport (MDW), which is located 8.4 mi (13.4 km) away from the heart of the city. Otherwise, you can search for flights to Chicago O'Hare Intl. Airport (ORD), which is 8.9 mi (14.3 km) away. If you'd like to explore around the area, you may want a rental car for your journey.